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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-18 09:06:02 UTC
Update Date2021-09-07 16:45:31 UTC
HMDB IDHMDB0001940
Secondary Accession Numbers
  • HMDB01940
Metabolite Identification
Common NameTriamterene
DescriptionTriamterene, also known as dyrenium or ademin, belongs to the class of organic compounds known as pteridines and derivatives. These are polycyclic aromatic compounds containing a pteridine moiety, which consists of a pyrimidine fused to a pyrazine ring to form pyrimido(4,5-b)pyrazine. Triamterene is a drug. While there is a lack of randomized controlled trials evaluating the use of triamterene in the treatment of Ménière's disease, the typical treatment is 37.5 mg of triamterene with 25 mg of hydrochlorothiazide 1-2 capsules daily. triamterene can be converted into triamterene through the action of the enzyme solute carrier family 22 member 2. In humans, triamterene is involved in the metabolic disorder called the triamterene action pathway. Triamterene directly blocks the epithelial sodium channel (ENaC) on the lumen side of the kidney collecting tubule. Hepatic impairment: Use with caution in people with severe hepatic dysfunction; in cirrhosis, avoid electrolyte and acid/base imbalances that might lead to hepatic encephalopathy. The patents had expired on Dyazide in 1980, but complications arose with the introductions of generics, because the formulation of Dyazide resulted in variable batches that made it impossible for generic manufacturers to show that their versions were bioequivalent.
Structure
Data?1582752218
Synonyms
ValueSource
TriamterenaChEBI
TriamterenumChEBI
DyreniumKegg
6-Phenyl-2,4,7-triaminopteridineHMDB
AdeminHMDB
AdemineHMDB
DirenHMDB
DitakHMDB
DiureneHMDB
DyrenHMDB
DytacHMDB
JatropurHMDB
NoridilHMDB
NoridylHMDB
PterofenHMDB
PteropheneHMDB
TaturilHMDB
TeriamHMDB
TeridinHMDB
Tri-spanHMDB
TriampurHMDB
TriamterenHMDB
TriamterilHMDB
Triamteril complexHMDB
TrispanHMDB
TriterenHMDB
Jorba brand OF triamtereneHMDB
SmithKline beecham brand OF triamtereneHMDB
Wellspring brand OF triamtereneHMDB
UrocaudalHMDB
Goldshield brand OF triamtereneHMDB
Chemical FormulaC12H11N7
Average Molecular Weight253.2626
Monoisotopic Molecular Weight253.107593387
IUPAC Name6-phenylpteridine-2,4,7-triamine
Traditional Nametriamterene
CAS Registry Number396-01-0
SMILES
NC1=NC(N)=C2N=C(C(N)=NC2=N1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C12H11N7/c13-9-7(6-4-2-1-3-5-6)16-8-10(14)18-12(15)19-11(8)17-9/h1-5H,(H6,13,14,15,17,18,19)
InChI KeyFNYLWPVRPXGIIP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pteridines and derivatives. These are polycyclic aromatic compounds containing a pteridine moiety, which consists of a pyrimidine fused to a pyrazine ring to form pyrimido(4,5-b)pyrazine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassNot Available
Direct ParentPteridines and derivatives
Alternative Parents
Substituents
  • Pteridine
  • Aminopyrazine
  • Aminopyrimidine
  • Monocyclic benzene moiety
  • Pyrazine
  • Pyrimidine
  • Benzenoid
  • Imidolactam
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Organopnictogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point316 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.98HANSCH,C ET AL. (1995)
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
AllCCS[M+H]+Not Available155.364http://allccs.zhulab.cn/database/detail?ID=AllCCS00000976
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.96 g/LALOGPS
logP10(1.21) g/LALOGPS
logP10(1.11) g/LChemAxon
logS10(-2.4) g/LALOGPS
pKa (Strongest Acidic)15.88ChemAxon
pKa (Strongest Basic)1.86ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area129.62 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity75.13 m³·mol⁻¹ChemAxon
Polarizability25.9 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+158.11331661259
DarkChem[M-H]-158.8931661259
AllCCS[M+H]+157.74632859911
AllCCS[M-H]-159.92132859911

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Triamterene CI-B (Non-derivatized)splash10-0udi-0090000000-c8bbcf103f5a3fdfebb52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Triamterene CI-B (Non-derivatized)splash10-0udi-0090000000-c8bbcf103f5a3fdfebb52018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Triamterene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w29-1290000000-6c14e74eed7c6b52485a2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Triamterene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene CI-B (Unknown) , Positive-QTOFsplash10-0udi-0090000000-c8bbcf103f5a3fdfebb52012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene LC-ESI-QTOF , positive-QTOFsplash10-0udr-0090000000-007b38b2c4832f3499092017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene LC-ESI-QTOF , positive-QTOFsplash10-000i-0590000000-b0551f41584c039101f62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene LC-ESI-QTOF , positive-QTOFsplash10-00kf-0910000000-6428faa965a39a470ea52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene LC-ESI-QFT , positive-QTOFsplash10-0udi-0090000000-c1e38db82ca2bfb168b72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene LC-ESI-QFT , positive-QTOFsplash10-0udi-0090000000-e0b752d624dade8793ef2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene LC-ESI-QFT , positive-QTOFsplash10-0udi-0090000000-4c12cffcdf72d196b5902017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene LC-ESI-QFT , positive-QTOFsplash10-0f79-0190000000-e63d14e64b8206d5c6352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene LC-ESI-QFT , positive-QTOFsplash10-0f79-0970000000-a69efa072a4b5fca04632017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene LC-ESI-QFT , positive-QTOFsplash10-0uxu-0910000000-f8ece9e1491b71df0c702017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene LC-ESI-QFT , positive-QTOFsplash10-0uxu-3900000000-946796a2530a51263ccd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene LC-ESI-QFT , positive-QTOFsplash10-0f79-9600000000-59b671ef134dd81063312017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene LC-ESI-QFT , positive-QTOFsplash10-0gw0-9200000000-3451a9c6dc2b3f4b6e3b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene , positive-QTOFsplash10-0udi-0190000000-425707e7729440a5bdb42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene , positive-QTOFsplash10-0udi-0190000000-32f8b6872d5877d003162017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene 45V, Positive-QTOFsplash10-0udi-0090000000-a14c539f152a7ab678752021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene 75V, Positive-QTOFsplash10-0f79-0970000000-fe05b51d696f50542dc02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene 60V, Positive-QTOFsplash10-0f79-0190000000-11a49ba5bf0ceb455fe22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene 90V, Positive-QTOFsplash10-0uxu-0910000000-68e1cc4a9e81f92b16e22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene 40V, Positive-QTOFsplash10-000i-0490000000-c81b5244938692d978e42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene 30V, Positive-QTOFsplash10-0udr-0090000000-c4e43e75d492d0f7ef6c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene 50V, Positive-QTOFsplash10-00kf-0910000000-7e907c521bda88db046b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene 75V, Positive-QTOFsplash10-0uy0-0950000000-9640d8d1b3c68318d31d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene 60V, Positive-QTOFsplash10-0f79-0190000000-07d05ef78d285d7a3a862021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triamterene 45V, Positive-QTOFsplash10-0udi-0090000000-53206da61b98c05436e32021-09-20HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00384
Phenol Explorer Compound IDNot Available
FooDB IDFDB022755
KNApSAcK IDNot Available
Chemspider ID5345
KEGG Compound IDD00386
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTriamterene
METLIN ID2908
PubChem Compound5546
PDB IDNot Available
ChEBI ID9671
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Remonda L, Frigerio SB, Buhler R, Schroth G: Transvenous coil treatment of a type a carotid cavernous fistula in association with transarterial trispan coil protection. AJNR Am J Neuroradiol. 2004 Apr;25(4):611-3. [PubMed:15090352 ]
  2. Weill A, Roy D, Georganos SA, Guilbert F, Raymond J: Use of the trispan device to assist coil embolization of high-flow arteriovenous fistulas. AJNR Am J Neuroradiol. 2002 Aug;23(7):1149-52. [PubMed:12169472 ]
  3. Yang TH, Wong HF, Yang MS, Ou CH, Ho TL: "Waffle cone"technique for intra/extra-aneurysmal stent placement for the treatment of complex and wide-necked bifurcation aneurysm. Interv Neuroradiol. 2008 Nov 11;14 Suppl 2:49-52. Epub 2009 Jan 2. [PubMed:20557801 ]
  4. Nakiri GS, Bravo E, Al-Khawaldeh M, Rivera R, Badilla L, Mounayer C: Endovascular treatment of aneurysm arising from fenestration of the supraclinoid internal carotid artery--two case reports. J Neuroradiol. 2012 Jul;39(3):195-9. doi: 10.1016/j.neurad.2011.10.001. Epub 2011 Dec 19. [PubMed:22189288 ]
  5. Dib M, Sedat J, Raffaelli C, Petit I, Robertson WG, Jaeger P: Endovascular treatment of a wide-neck renal artery bifurcation aneurysm. J Vasc Interv Radiol. 2003 Nov;14(11):1461-4. [PubMed:14605114 ]
  6. Turk AS, Rappe AH, Villar F, Virmani R, Strother CM: Evaluation of the TriSpan neck bridge device for the treatment of wide-necked aneurysms: an experimental study in canines. Stroke. 2001 Feb;32(2):492-7. [PubMed:11157188 ]
  7. Henkes H, Kirsch M, Mariushi W, Miloslavski E, Brew S, Kuhne D: Coil treatment of a fusiform upper basilar trunk aneurysm with a combination of "kissing" neuroform stents, TriSpan-, 3D- and fibered coils, and permanent implantation of the microguidewires. Neuroradiology. 2004 Jun;46(6):464-8. Epub 2004 Apr 22. [PubMed:15103433 ]
  8. Bradac GB, Bergui M, Stura G, Fontanella M, Daniele D, Gozzoli L, Berardino M, Ducati A: Periprocedural morbidity and mortality by endovascular treatment of cerebral aneurysms with GDC: a retrospective 12-year experience of a single center. Neurosurg Rev. 2007 Apr;30(2):117-25; discussion 125-6. Epub 2007 Jan 11. [PubMed:17216530 ]
  9. Cil BE, Erdogan C, Akmangit I, Cekirge S, Balkanci F: Use of the TriSpan coil to facilitate the transcatheter occlusion of pulmonary arteriovenous malformation. Cardiovasc Intervent Radiol. 2004 Nov-Dec;27(6):655-8. [PubMed:15593430 ]
  10. Schroth G, Lovblad KO, Ozdoba C, Remonda L: Non-traumatic neurological emergencies: emergency neuroradiological interventions. Eur Radiol. 2002 Jul;12(7):1648-62. Epub 2002 May 18. [PubMed:12111055 ]
  11. Chan DT, Boet R, Yu S, Poon WS: Trispan-assisted coiling of a wide-necked Persistent Trigeminal Artery aneurysm. Acta Neurochir (Wien). 2004 Jan;146(1):87-8; discussion 88. Epub 2003 Dec 15. [PubMed:14740272 ]

Enzymes

General function:
Involved in ligand-gated sodium channel activity
Specific function:
Sodium permeable non-voltage-sensitive ion channel inhibited by the diuretic amiloride. Mediates the electrodiffusion of the luminal sodium (and water, which follows osmotically) through the apical membrane of epithelial cells. Controls the reabsorption of sodium in kidney, colon, lung and sweat glands. Also plays a role in taste perception
Gene Name:
SCNN1A
Uniprot ID:
P37088
Molecular weight:
75703.1
General function:
Involved in ligand-gated sodium channel activity
Specific function:
Sodium permeable non-voltage-sensitive ion channel inhibited by the diuretic amiloride. Mediates the electrodiffusion of the luminal sodium (and water, which follows osmotically) through the apical membrane of epithelial cells. Controls the reabsorption of sodium in kidney, colon, lung and sweat glands. Also plays a role in taste perception
Gene Name:
SCNN1G
Uniprot ID:
P51170
Molecular weight:
74269.6
General function:
Involved in ligand-gated sodium channel activity
Specific function:
Sodium permeable non-voltage-sensitive ion channel inhibited by the diuretic amiloride. Mediates the electrodiffusion of the luminal sodium (and water, which follows osmotically) through the apical membrane of epithelial cells. Controls the reabsorption of sodium in kidney, colon, lung and sweat glands. Also plays a role in taste perception
Gene Name:
SCNN1B
Uniprot ID:
P51168
Molecular weight:
72658.5
General function:
Involved in ligand-gated sodium channel activity
Specific function:
Sodium permeable non-voltage-sensitive ion channel inhibited by the diuretic amiloride. Mediates the electrodiffusion of the luminal sodium (and water, which follows osmotically) through the apical membrane of epithelial cells. Controls the reabsorption of sodium in kidney, colon, lung and sweat glands. Also plays a role in taste perception
Gene Name:
SCNN1D
Uniprot ID:
P51172
Molecular weight:
70214.2